a long talk

‘I Believe He Will Lose It Big’

David Letterman talks Trump, being wrong in 2016, and his late-night legacy.

David Letterman in My Next Guest Needs No Introduction. Photo: Mathieu Bitton/Netflix
David Letterman in My Next Guest Needs No Introduction. Photo: Mathieu Bitton/Netflix

David Letterman has been interviewing people for a living for nearly 40 years, so it’s not surprising that a phone call with him would start off with some small talk. “Tell me about Las Vegas,” the late-night legend says, inquiring about the city where I grew up. He wants to know how the Las Vegas Raiders’ Allegiant Stadium fits into the skyline (“I was there a couple of years ago and saw the skeleton of it,” he notes); what I think of the amazing success of the Golden Knights hockey team (“That to me is a remarkable story,” he gushes); and what the weather is like where I am right now.

When Letterman moved to CBS from NBC back in 1993, the network ran promos in which its new host informed viewers, with somewhat mock sincerity, “I want to be your TV friend.” Twenty seven years later, and five years after his final Late Show was broadcast, Letterman’s interest feels completely genuine. “I always like to find out what is going on in other parts of the country and especially places I have some familiarity with,” he says. After a little more small talk, Letterman and I moved on to more pressing topics, including his prediction for how this week’s election will turn out, his regrets over how he handled his professional relationship with Donald Trump, and the reason why our 20-minute phone conversation had been scheduled: the recent return of his acclaimed Netflix talk show My Next Guest Needs No Introduction.

Are you in New York right now, or are you in Montana?
I’m in Westchester, not Montana. Montana’s got a foot of snow and it was like five degrees yesterday, which is also quite unusual this time of year. The good thing about getting that much snow now: It puts an end to the fire season. And I guess, sadly, the fire season in California is pretty much year-round now. But in Montana, the snow signals the end of that.

Well, that’s good. If they would just rake the leaves more in California, they’d be fine with their fires.
I’ve been after them to just get out there. I mean, people enjoy raking leaves, I know I do. Turn me loose with a rake and a hundred-thousand acres of forest land and that’s my weekend.

There you go. Well, that’s a good transition to my first question. Back in October 2016, you said at The New Yorker Fest that there was “not a chance in hell” Donald Trump would win, but that if he did, “I’ll get you all a lovely gift from Tiffany’s.” So how are you feeling right now?
I was very certain of that because I heard Thomas Friedman say that. No, it wasn’t Thomas Friedman. It was the guy on the PBS NewsHour, the Republican pundit, David Brooks. He had said that he would win the primaries but be crushed in the general. And I thought, Okay, David Brooks. Yeah, okay. That’s good enough for me. Well, that didn’t happen. It was sort of a coin flip because of the popular versus the electoral vote. And if you were there I’m sorry, but I did buy everyone earrings. Now, if you didn’t get them, then … [shouting to imaginary assistant] “He didn’t get his earrings!” We’ll get them right out to you, Joe. [Letterman’s dog starts barking.] Geez, now there’s my dog.

So what about the 2020 results?
I believe he will lose it big, and it will be a relief to every living being in this country, whether they realize it now or not. It certainly will be a relief to me and my family, and I think generally the population. I’m more confident now than I was then, and I was pretty confident then. I was wrong. I don’t think I’ll be wrong this time.

Has there been sort of a low point for you during the four years of the Trump administration?
Well, I’ll tell you when it really began was when he declared that the press was the enemy of the people. And to me, this seemed like something you hear coming out of Venezuela, when Hugo Chávez was running that country. I thought, This is not right. Even ill-informed people like myself know that this is not right. The press is not the enemy of the people. The press educates the people. The press informs the people. The press does the heavy lifting for people who don’t need to be aware of every single thing that’s going on because the press is doing that job for them.

So to single them out as the enemy for the people, that’s when I really thought, Oh my God. Having said that, as we know, things have gotten worse. But I’m tired of criticizing the president. I’m tired of criticizing the administration. I’m tired of moaning and hand-wringing. I think this man is a bully, and bullies frighten people. But just by voting, I think that’s going to be the end of it. Then I think the real fun will begin — to see what transpires after this job is taken out from under him.

You’ve talked before about how you maybe regretted your fake apology to Trump for calling him a racist. You said you did it because he made for great TV. I imagine you did a lot of things in the quest to make the show better, but would you still do all those things now? Any regrets?
Well, yeah, that’s a long list of things that I regret and would not have done knowing what I know now. But, specifically with regard to Trump, I feel like I should have stuck by my accusation and not have caved to get him back on the show. I had to do a nightly show, and I didn’t know then what I know now. I should’ve known more about what he was up to, but I just didn’t. I have always sort of felt that smart people were not racists. I didn’t know that it seemed to be genetic in his case.

Let’s talk about the new season of the Netflix show. You did stand-up when you went to interview Dave Chappelle in Ohio. Was it odd going back and flexing those muscles again, even if only for a few minutes?
I was intimidated because I had to sit through, I don’t know, I think four or five men or women that were on the show. And [Chappelle] was the emcee. If Dave Chappelle is the emcee, you’re reluctant to get out of the car. But it just built and Dave was funny, and the first act was funny, and then the second act was funnier, and then Dave was funnier and on and on and on and on. I just kept thinking, Well, why am I here? It was in an open field, surrounded by woods, and I thought, I really should just disappear into the woods here now.

Then the next thing you know, Dave is introducing me. I go out there, and he handled it remarkably well — superbly, as a matter of fact. He made the audience there feel like I belonged onstage with him. He was so generous and so supportive that my little two or three minutes was just fine. But I’m telling you, if I had to go on up there without Dave, it would have been a struggle. But he was a big, big help, and not everybody in show business is that eager to help another performer — and I use “performer” with regard to me loosely. But it was a great night and it was one of the coolest things I got to do in a long time, and especially right in the middle of the horror of the pandemic running crazy around the world. It was a nice respite, but all credit to Dave Chappelle. He’s really a master.

Did it reawaken any sense of you wanting to do more stand-up? I mean, I remember Barbra Streisand, Carly Simon — for the longest time, they didn’t perform in public, and then they did a couple of performances, and soon they were back onstage more regularly.
Let me just say that you comparing me to Carly Simon and Barbra Streisand has put me on the moon. Thank you, and I think we’re finished here. I mean, there’s your headline, come on. And the answer is, no.

At the end of your episode with Chappelle, he talks a lot about how much you inspired him. A lot of modern comedy figures talk about how much of an inspiration you were to them. You yourself are one of the most famous fans of Johnny Carson, and for years you would talk about how important he was. You occupy that Carson space for a different generation. Are you now okay with that sort of veneration?
Well, I used to hate it because it made me self-conscious. I believed in my heart I was not worthy of it. Because when you’re doing a television show, that’s all you’re looking at. You’re looking at the TV show and the audience and the material and the guests, and that’s all. Now that I have essentially passed away, to see it and to hear … When you hear something like this from Dave Chappelle, you can’t take it lightly because he’s a very wise fellow, and it was highly meaningful. To me, it also kind of reset my focus on what I hear from others like Jimmy Kimmel, who I consider a friend now, and men and women who have said essentially the same thing. And I feel, I don’t know … I’m sort of starting to kind of find that as maybe the most pleasing aspect of my career.

You’ve never been on Saturday Night Live. Has Lorne Michaels asked you, and you’ve said no?
Lorne Michaels, who, I mean, my goodness, there’s someone — I mean, he’s NASA to comedy, this guy. Early on we worked in the same building and he did ask me, I think, once or twice, and I was scared silly. I had done a variety show with Mary Tyler Moore for one summer in California, so I kind of knew what the drill was. And I was so certain, absolutely positive, that I would screw up his show and have to continue working with him in the same building that I said, “Oh, geez, I’m very sorry.” And I never did it. Now, I think they do such a nice job of supporting the guests there that I probably wouldn’t have put them out of business. It’s a small regret that that was not part of my life, because you see other people who have long, long relationships with Lorne and that show, and I think that’s a mark of a great career. I don’t have that, but it was my own foolishness.

Betty White came on in her 90s. If you were asked now, do you think you’d say yes?
Oh, God, no. Unless I get to go on with Barbra Streisand and Carly Simon, and we would sing one of our famous trios. Duets? No, that’s three. You know what I’m talking about, Joe.

What’s your pop-culture consumption like right now, especially during the pandemic? Do you watch a lot of television or movies? Is it all news? Do you find ways to keep up with who’s hot in comedy right now? 
Not as much as I did when I was working, because when you’re working, you’re in that solar system. But not working, you have to go and look for it. I came across something the other day, which apparently I didn’t realize is a genre of presentation on YouTube, and I was delighted by it. It’s two twins. I believe they live in Gary, Indiana, and they listen to music for the first time — music that, for me, and I think probably for you, was typical growing-up music we’re all aware of. But these kids, because of their age, had never heard of it, and they listened to it for the first time and then they react to it. And I found these two guys to be so, just sweet and lovely, and their reaction to this music is delightful. So that was my latest entry into the world of social media and pop culture. And if that’s what it is, I’ll take all of that I can get. Do you know who I’m talking about?

I do. I’ve seen them. The one with “In the Air Tonight” by Phil Collins was amazing.
Oh, my goodness. Yeah. And then like everything else, you keep watching and watching and watching. Before the internet and social media, you really had to work hard to learn about culture that came before you. But here, you see it demonstrated by these kids and others, and I found it touching and entertaining and just delightful.

I’ve wondered whether Tom Snyder was at all an inspiration for what you’re trying to do with the Netflix series. Not his interview style, but just the idea of deep-dive interviews like the ones he did on Tomorrow and the CBS show you produced with him. 
When I worked in local television at the ABC affiliate in Indianapolis, Indiana, Channel 13, WLWI, and we would sign off, I would go home and the only thing that was on then, by the time I got home, was the Tomorrow show with Tom Snyder. Tom was going through his Edward R. Murrow phase, where it was just Tom in a chair with a cigarette and the smoke curling up beside him the way I remember Ed Murrow presenting himself when he would do the interviews with celebrities. It was House to House or Person to Person, or You Are There or Answer the Door, or whatever the show was. Then I had a show at the local TV station at the time, and what I was doing then was exactly Tom Snyder. I was talking like him. My phraseology was the same. My eyebrow work was quite similar, and I took it very earnestly. So you have detected something here that probably went latent for quite a few decades, but it may in fact be part of what we’re doing now, yeah. How about that? Because at one time, Tom subsumed my personality.

I think your interview style now is very much David Letterman, though …
Yeah. But they talk about that in many creative endeavors: Find somebody that you like or admire the work of and just imitate them. I think that was an early building block, as much as Carson or Steve Allen when it came to sitting down and talking to people on TV. Because I would race home every night, and there at 1 a.m. would be Tom Snyder for an hour. So it made an impact on me, and I think the association, while maybe not A [to] B, is certainly, at the very least, an indirect connection.

You mentioned Mary Tyler Moore, and I’ve lately become obsessed with watching The Mary Tyler Moore Show
Well, look, this is interesting. A friend of mine is also just coming to The Mary Tyler Moore Show now. I worked at an ABC affiliate, and we had a lobby television that carried all of the ABC shows. On Saturday night we would get the engineers up there to rewire the television so we could watch the CBS lineup, and it was Bob Newhart and Mary Tyler Moore. Now you tell me: Weren’t those shows, and aren’t those shows, still today superior to what is the version of situation comedy on television these days?

A thousand percent.
Now, I haven’t seen it in ten years or so, but I used to watch [Mary Tyler Moore] all the time when it was rerun on … maybe it was Nick at Nite. But I fell in love with that all over again. I can remember Ted Baxter — they’re all getting ready to go to lunch. And of course, nobody wants to go to lunch with Ted Baxter and Ted Baxter walks in and says [in Ted Baxter anchorman voice], “Hi, Lou. Hi, Mary. Hi, Murray. What are you guys doing?” “Oh, we’re going to lunch, Ted.” “Oh, where are you going to have lunch?” “Well, we’re going to go to that new Mexican restaurant around the corner.” And Ted says, “Oh, I haven’t had New Mexican food since I was in Albuquerque.” And I thought, Come on. Honest to God, that’s as good as you’re going to get. It was tremendous. If you had to sell a show, you could sell it on that one line. I don’t think in the half-hour form, there’s been anything — maybe things as funny, certainly not funnier.

What was it like to then get to work with Mary?
First of all, I had no business being on that show. I couldn’t have been happier, because that was like a big deal. It was an hour with Mary Tyler Moore, legitimately America’s sweetheart. We came on Sunday nights, right after 60 Minutes. Then my heart started to sink every Wednesday when the choreographer would come in. What that meant was, “All right, guys, we have to learn the new song-and-dance routine for the show.” A couple of times they found me unconscious in a rental car out in the parking lot. But luckily, I was revived and I realized, I don’t think I belong here, but that was a huge thing for them to have done for me. Because when I left, I got to keep my wardrobe.

Variety shows were almost on their way out by 1978. You also had a small career in game shows, too. I love watching you on Password and Pyramid. Your game-show work, David.
Oh, my game-show work. I just want to say, speaking of Betty White, then speaking of Allen Ludden: Liar’s Club. Those people had me on there like once a month, and I loved that show. It was delightful. And again, nobody ever knew who I was, which was fine. But so many people gave me opportunities that I just, now thinking about them, realize how much I really cherish those experiences. For God’s sake, if you think about the people I was working with, and they allowed me to do that. That was great because I was just a dope from Indiana. Still am, by the way.

David Letterman Thinks Trump Will ‘Lose It Big’